Sodium Hydroxide → [2-(tert-Butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amine

HRID 349518Notes

Reaction equation

HRID 349518 reaction equation
[Si:1]([O:8][CH2:9][CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:12]1([CH2:15][NH2:16])[CH2:14][CH2:13]1.[BH4-].[Na+].[OH-].[Na+]>CO>[Si:1]([O:8][CH2:9][CH2:10][NH:16][CH2:15][CH:12]1[CH2:14][CH2:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 75646CyclopropanemethanamineHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 69361897[2-(tert-Butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(tert-Butyldimethylsilyloxy)acetaldehyde (0.98 g) was dissolved in dry methanol (40 ml) and then treated with cyclopropane methylamine (0.634 ml) followed by 4A° molecular sieves (1 g). The resultant mixture was stirred for 5 h at room temperature and then sodium borohydride (0.340 g) was added. After stirring for a further 18 h at room temperature, sodium hydroxide (2N) was added, the mixture was filtered and the filtrate concentrated under reduced pressure. The residue was partitioned between sodium hydroxide (2N) and ethyl acetate. The separated aqueous layer was washed further with ethyl acetate. The combined organic components were dried (over magnesium sulphate), filtered and concentrated under reduced pressure to give the title compound (0.78 g) as a yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was partitioned between sodium hydroxide (2N) and ethyl acetate
  4. washThe separated aqueous layer was washed further with ethyl acetate
  5. dry with materialThe combined organic components were dried (over magnesium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be8638c430b34bc7ac9e1b29a068c19c
Source dataset
uspto-grants-2007_02
Patent number
US07179835B2

Reaction notes

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