Sodium triacetoxyborohydride → HCID 123503309, compound

HRID 2202683Notes

Reaction equation

HRID 2202683 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=O.[F:17][C:18]([F:25])([F:24])[C:19]1([CH2:22][NH2:23])[CH2:21][CH2:20]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:10][NH:23][CH2:22][C:19]1([C:18]([F:25])([F:24])[F:17])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 67148810HCID 67148810, compoundHCID 123439779HCID 123439779, compound

Product 1

HCID 123503309HCID 123503309, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 2-(2,6-dichlorophenyl)-2-((trimethylsilyl)oxy)acetaldehyde (0.35 g, 1.263 mmol) in DCM (6.31 ml) was added (1-(trifluoromethyl)cyclopropyl)methanamine (0.176 g, 1.263 mmol) and NaBH(OAc)3 (0.374 ml, 2.53 mmol) and stirred for 2 h at ambient temperature. The reaction was quenched with aqueous sat NH4Cl solution and diluted with DCM (50 mL). Organic layer was passed through phase separator and concentrated to obtain 2-(2,6-dichlorophenyl)-N-((1-(trifluoromethyl)cyclopropyl)methyl)-2-((trimethylsilyl)oxy)ethanamine (0.378 g, 70%) as light yellow oil. This was used in next step without further purification.

Workup

  1. customThe reaction was quenched
  2. additiondiluted with DCM (50 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1f7c2fda4c934aa482d27dcffe63f4de
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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