2-(Boc-amino)-3-(Cbz-amino)-1-propanol → tert-butyl N-(1-amino-3-hydroxypropan-2-yl)carbamate

HRID 1504849Notes

Reaction equation

HRID 1504849 reaction equation
[OH:1][CH2:2][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:4][NH:5]C(=O)OCC1C=CC=CC=1.[H][H]>CO>[NH2:5][CH2:4][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 755959732-(Boc-amino)-3-(Cbz-amino)-1-propanolHCID 178418361HCID 178418361, compound

Product 1

HCID 86731719tert-butyl N-(1-amino-3-hydroxypropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl tert-butyl (3-hydroxypropane-1,2-diyl)biscarbamate (400 mg, 1.23 mmol) was dissolved in methanol (12.3 mL) and put under a hydrogen atmosphere with 3 cycles of evacuation and hydrogen balloon flushing. The reaction mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours, and then filtered through CELITE. The filtrate was concentrated under reduced pressure to afford tert-butyl 1-amino-3-hydroxypropan-2-ylcarbamate. MS ESI calcd. for C8H19N2O3 [M+H]+ 191. found 191. 1H NMR (500 MHz, CDCl3) δ 5.25 (s, 1H), 3.87 (d, J=10.0 Hz, 1H), 3.71 (d, J=10.5 Hz, 1H), 3.59-3.63 (m, 1H), 3.08 (d, J=10.6 Hz, 1H), 2.90 (d, J=10.1 Hz, 1H), 1.84 (s, 2H), 1.45 (s, 9H).

Workup

  1. customflushing
  2. filtrationfiltered through CELITE
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b05e930550c471bb9e7598f69bc5ef5
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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