Lithium borohydride → Carbamic acid, [(1R)-1-(2-hydroxyethyl)-2-methylpropyl]-, 1,1-dimethylethyl

HRID 276264Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:15]([CH3:17])[CH3:16])[CH2:10][C:11](OC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 4148881Lithium borohydride

HCID 15474577HCID 15474577, compound

Product 1

HCID 11715497Carbamic acid, [(1R)-1-(2-hydroxyethyl)-2-methylpropyl]-, 1,1-dimethylethylYield 93%

Procedure

Methyl (R)-3-(tert-butoxycarbonylamino)-4-methylpentanoate (1.62 g, 6.6 mmol) was treated with lithium borohydride in a manner analogous to Method B8a, Step 2 to afford (R)-3-(tert-butoxycarbonylamino)-4-methylpentanol (93%).

Sources & evidence

ORD record: ord-06dfa509d77b4aa88d7e6103c35565cf
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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