Tetrahydrofuran → tert-Butyl [(2R)-1-chloro-3-hydroxypropan-2-yl]carbamate

HRID 714143Notes

Reaction equation

HRID 714143 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12](OC)=[O:13])[CH2:10][Cl:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-].C1COCC1.C([O-])(O)=O.[Na+]>C(O)C.C(Cl)Cl.CC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:12][OH:13])[CH2:10][Cl:11])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 12182794METHYL N-BOC-3-CHLORO-L-ALANINATE

Product 1

HCID 12184455tert-Butyl [(2R)-1-chloro-3-hydroxypropan-2-yl]carbamate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl N-(tert-butoxycarbonyl)-3-chloro-L-alaninate (56, 2.13 g, 9.0 mmol) in ethanol (41 ml) stirred at 0° C. under N2 atmosphere was treated with a 2M solution of LiBH4 in THF (5 mL, 10 mmol) (slow addition). The reaction mixture was slowly warmed up to room temperature and further stirred for 4 h, cooled to 0° C., treated with saturated NaHCO3 (5 mL) followed by acetone (5 mL), stirred for 10 minutes, diluted with DCM and washed with brine, dried over MgSO4 filtered and concentrated to afford 1.94 (100% yield) of title compound as a white solid. MS: m/z=232.0 (MNa+).

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred for 10 minutes
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-564de3112be6413b8f6974f705081fc1
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

Loading…