Lithium borohydride → 2-(Boc-amino)-3-(Cbz-amino)-1-propanol

HRID 1504843Notes

Reaction equation

HRID 1504843 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([C:22](OC)=[O:23])[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>C1COCC1.O>[OH:23][CH2:22][CH:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 15092375Methyl (2S)-3-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}propanoate

Product 1

HCID 755959732-(Boc-amino)-3-(Cbz-amino)-1-propanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alaninate (80 g, 230 mmol) in THF (800 mL) was added lithium borohydride (20 g, 920 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 1 hour, the reaction mixture was diluted with water and filtered. The filtrate was concentrated under reduced pressure to give benzyl tert-butyl (3-hydroxypropane-1,2-diyl)biscarbamate. MS ESI calc'd. for C16H25N2O5 [M+H]+ 325. found 325. 1H NMR (400 MHz, CDCl3) δ 7.38-7.35 (m, 5H), 5.11 (s, 2H), 4.70 (s, 1H), 4.13-4.11 (m, 1H), 3.66-3.28 (m, 4H), 2.04 (s, 2H), 1.43 (s, 9H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6f47e59b435d445b8ad4f3a18b1ba3ea
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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