1,1-Dichloroethane → [2-(Tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentylamine

HRID 2169320Notes

Reaction equation

HRID 2169320 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Si:5]([O:12][CH2:13][CH:14]=O)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[BH4-].[Na+].Cl[CH:19](Cl)[CH3:20]>C(O)(=O)C>[Si:5]([O:12][CH2:13][CH2:14][NH:4][CH:1]1[CH2:20][CH2:19][CH2:2][CH2:3]1)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 69828CyclopropylamineHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 86725959[2-(Tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentylamineYield 37.48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a stirred solution of cyclopropylamine (1 g, 13.15 mmol) in dichlorethane (20 mL) were added 2-(tert-butyl-dimethylsilanyloxy)acetaldehyde (2.3 mg, 2.30 mmol) and acetic acid (0.08 mL, 0.29 mmol) at 0° C. Stirring was continued for 24 h at room temperature and NaBH4 (995 mg, 26.29 mmol) was added portion-wise at 0° C. The reaction mixture was further stirred for 2 h at room temperature, quenched with water and extracted with dichloromethane (3×30 mL). The organic part was dried and concentrated to yield a crude product which was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to get [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentylamine (8e) (1.2 g, 37.48%) as a yellow oil.

Workup

  1. stirringThe reaction mixture was further stirred for 2 h at room temperature
  2. customquenched with water
  3. extractionextracted with dichloromethane (3×30 mL)
  4. customThe organic part was dried
  5. concentrationconcentrated
  6. customto yield a crude product which
  7. customwas purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f47caab5cbfd4c2097a8cbdf4a246e4e
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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