Carbamic acid, [(3S,5S)-5-(hydroxymethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl

Base Information

• Chemical Name: Carbamic acid, [(3S,5S)-5-(hydroxymethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl
• CAS No.: 663948-85-4
• Molecular Formula: C10H20N2O3
• Molecular Weight: 216.28
• Mol file: 663948-85-4.mol

Synonyms:Carbamic acid, [(3S,5S)-5-(hydroxymethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl;tert-butyl (3S,5S)-5-(hydroxymethyl)pyrrolidin-3-ylcarbamate;(2S,4S)-2-hydroxymethyl-4-BOC-amino Pyrrolidine-HCL;

Chemical Property of Carbamic acid, [(3S,5S)-5-(hydroxymethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl

Chemical Property:

• Refractive Index: 1.5
• Boiling Point: 351.4 °C at 760 mmHg
• PKA: 12.21±0.40(Predicted)
• Flash Point: 166.3 °C
• PSA: 70.59000
• Density: 1.11 g/cm³
• LogP: 0.95360
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl ((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate, can be used in the synthesis of various pharmaceutical and biologically active compounds. It can be used in the preparation of new chiral building blocks for novel peptide nucleic acids.

Technology Process of Carbamic acid, [(3S,5S)-5-(hydroxymethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl

There total 8 articles about Carbamic acid, [(3S,5S)-5-(hydroxymethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzyl (2S,4S)-4-((tert-butoxycarbonyl)amino)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (380648-94-2) → tert-butyl ((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate (663948-85-4,1070295-74-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1081/NCN-100002517

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → tert-butyl ((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate (663948-85-4,1070295-74-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / pyridine / cooling

2: 98.5 percent / NaN₃ / dimethylformamide / 8 h / 70 °C

3: H₂ / Raney Nickel / methanol; H₂O / 1.5 h / 2068.59 Torr

4: 3.17 g / Et₃N / dimethylsulfoxide / 8 h

5: 70 percent / LiBH₄ / tetrahydrofuran / 3.5 h

6: H₂ / Pd-C / methanol / 7 h / 3102.89 Torr

With pyridine; lithium borohydride; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00331-6

Reference yield:

4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester (113490-74-7) → tert-butyl ((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate (663948-85-4,1070295-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Raney Nickel / methanol; H₂O / 1.5 h / 2068.59 Torr

2: 3.17 g / Et₃N / dimethylsulfoxide / 8 h

3: 70 percent / LiBH₄ / tetrahydrofuran / 3.5 h

4: H₂ / Pd-C / methanol / 7 h / 3102.89 Torr

With lithium borohydride; hydrogen; triethylamine; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; water; dimethyl sulfoxide;

DOI:10.1016/S0968-0896(03)00331-6

upstream raw materials:

benzyl (2S,4S)-4-((tert-butoxycarbonyl)amino)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate

Downstream raw materials:

{(2S,4S)-4-t-butoxycarbonylamino-1-[(thymin-1-yl)methylcarbonyl]-pyrrolidin-2-yl}methyl 4-nitrophenyl carbonate

carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester

C₃₉H₅₁N₅O₁₁

benzyl (2S,11S,19aS)-2-(acetylamino)-15-fluoro-7,12-dimethyl-5,8,13-trioxo-2,3,6,7,8,9,10,11,12,13,19,19a-dodecahydro-1H,5H-pyrrolo[2,1-c][1,4,7,12]benzoxatriazacyclopentadecine-11-carboxylate