Lithium borohydride → Tert-Butyl(1-(Hydroxymethyl)cyclopropyl)methylcarbamate

HRID 496061Notes

Reaction equation

HRID 496061 reaction equation
[BH4-].[Li+].[C:3]([O:7][C:8]([N:10]([CH3:18])[C:11]1([C:14](OC)=[O:15])[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1.CCOCC>[OH:15][CH2:14][C:11]1([N:10]([CH3:18])[C:8](=[O:9])[O:7][C:3]([CH3:4])([CH3:5])[CH3:6])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 22325133Methyl 1-[[(1,1-dimethylethoxy)carbonyl]methylamino]cyclopropanecarboxylate

Product 1

HCID 52988048Tert-Butyl(1-(Hydroxymethyl)cyclopropyl)methylcarbamate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

100 ml of a 2M solution of lithium borohydride in tetrahydrofuran is added to a solution of 23 g of the compound obtained in Step 2 in 100 ml of tetrahydrofuran. After stirring for 20 hours at ambient temperature and then refluxing for 8 hours, the reaction mixture is cooled to 0° C., hydrolysed, diluted with ether, separated, dried and concentrated. Chromatography of the residue over silica gel (dichloromethane/tetrahydrofuran: 95/5) allows the expected product to be isolated.

Workup

  1. temperaturerefluxing for 8 hours
  2. temperaturethe reaction mixture is cooled to 0° C.
  3. customseparated
  4. customdried
  5. concentrationconcentrated
  6. customto be isolated

Sources & evidence

ORD record
ord-5fb77eb273774e15a4e64a3b0abb9ee1
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

Loading…