Lithium borohydride → tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

HRID 620148Notes

Reaction equation

HRID 620148 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH:13]([CH3:15])[CH3:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[BH4-].[Li+]>COCCOC>[C:9]([O:8][C:6]([NH:5][C@H:4]([CH2:3][OH:2])[CH:13]([CH3:14])[CH3:15])=[O:7])([CH3:11])([CH3:12])[CH3:10]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 11031717N-(tert-Butoxycarbonyl)-L-valine methyl ester

Product 1

HCID 7021464tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamateYield 81%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

This compound was prepared in 81% yield from the ester 4b (9.28 g, 40 mmol) by reduction with lithium borohydride in dry DME following the procedure that has been described earlier1,2. TLC Rf 0.47 (eluent MeOH/CHCl3,7/93). 1H NMR (CDCl3) δ 0.91 and 0.98 (dd, J=2 Hz, 6H, CH3CHCH3), 1.44 (s, 9H, t-Bu), 1.45-1.97 (m, 1H, CH3CHCH3), 2.15 (s, 1H, OH), 3.24-3.49 (m, 1H, CHCH2), 3.53-3.72 (m, 2H, CH2OH), 4.36-4.77 (m, 1H, NH). CI MS, m/e 204 (M+ +1).

Sources & evidence

ORD record
ord-29c26da8a0be4c3a8095f527ddb78703
Source dataset
uspto-grants-1989_04
Patent number
US04820712

Reaction notes

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