Water → tert-butyl [(2R)-2-methoxypropyl]carbamate

HRID 1910398Notes

Reaction equation

HRID 1910398 reaction equation
[OH:1][C@H:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:13]N(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.F[B-](F)(F)F.C[O+](C)C.O>C(Cl)Cl>[CH3:13][O:1][C@H:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 12094522N-Boc-(R)-1-amino-2-propanol

Product 1

HCID 86641515tert-butyl [(2R)-2-methoxypropyl]carbamateYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(2R)-2-hydroxypropyl]carbamate (2.7 g) in CH2Cl2 (41 ml) were added N,N,N′,N′-tetramethylnaphthalene-1,8-diamine (3.63 g) and trimethyloxonium tetrafluoroborate (2.51 g), and the whole was stirred for 3 hours at room temperature. Water was added to the mixture, and the whole was extracted with EtOAc, and the extract was washed with water and brine and dried over MgSO4. Concentration under reduced pressure gave tert-butyl [(2R)-2-methoxypropyl]carbamate (2.73 g).

Workup

  1. extractionthe whole was extracted with EtOAc
  2. washthe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-85518414f53d4eac964b9ef51eb66f51
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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