Lithium borohydride → N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanol

HRID 620149Notes

Reaction equation

HRID 620149 reaction equation
C[O:2][C:3](=O)[C@H:4]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[BH4-].[Li+].CO.C(Cl)(Cl)Cl>COCCOC>[C:9]([O:8][C:6]([NH:5][C@H:4]([CH2:3][OH:2])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:7])([CH3:10])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 4148881Lithium borohydrideHCID 11791441Boc-L-isoleucine methyl esterHCID 21584188Chloroform methanol

Product 1

HCID 14237729N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanolYield 97%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

This compound was prepared in 97% yield from the ester 4c (9.84 g, 40 mmol) by reduction with lithium borohydride in dry DME analogous to the method described earlier1,2. TLC Rf 0.47 (eluent MeOH/CHCl3, 7/93). 1H NMR (CDCl3) δ 0.83-1.03 (m, 6H, CHCH3, CH2CH3), 1.03-1.40 (m, 2H, CH2CH3, CH2CH3), 1.44 (s, 9H, t-Bu), 2.21-2.61 (m, 1H, CHCH3), 3.32-3.88 (m, 4H, CHCH2OH), 4.52-4.68 (m, 1H, NH), CI MS, m/e 218 (M+ +1).

Sources & evidence

ORD record
ord-a09d34ff561641d9927054c420ae2296
Source dataset
uspto-grants-1989_04
Patent number
US04820712

Reaction notes

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