Water → tert-butyl N-((2R)-3-hydroxy-2-methylpropyl)carbamate

HRID 1434848Notes

Reaction equation

HRID 1434848 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH3:14])[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C)C.B.C1COCC1.O>C1COCC1.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH3:14])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 2723981Borane;tetrahydrofuranHCID 11041840(R)-3-((tert-butoxycarbonyl)amino)-2-methylpropanoic acid

Product 1

HCID 10655267tert-butyl N-((2R)-3-hydroxy-2-methylpropyl)carbamateYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. mixture of (2R)-3-t-butoxycarbonylamino-2-methylpropionic acid (4.6 g, 21.0 mmol) in THF (100 mL) was added 2 M Me2S.BH3/THF (16 mL, 31.5 mmol, 1.5 equivalents). After stirring for 2 h, water was added and the mixture stirred for 18 h. The mixture was diluted with CH2Cl2 and washed with satd Na2CO3. The organic layer was dried (Na2SO4), concentrated, and chromatographed (CH2Cl2; EtOAc) to give the title compound as an oil (2.4 g, 61%).

Workup

  1. stirringthe mixture stirred for 18 h
  2. washwashed with satd Na2CO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (CH2Cl2; EtOAc)

Sources & evidence

ORD record
ord-2b494a6a528a473cad84ab2bf30c465c
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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