Pivalaldehyde → HCID 21182945, compound

HRID 377414

Reaction equation

HRID 377414 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:33]=[CH:32][C:12]([CH2:13][C:14]3[C:15]4[CH:31]=[CH:30][CH:29]=[CH:28][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH2:27])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:34][C:35]([CH3:39])(C)[CH:36]=O.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:33]=[CH:32][C:12]([CH2:13][C:14]3[C:15]4[CH:31]=[CH:30][CH:29]=[CH:28][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:40][CH2:36][CH:35]([CH3:39])[CH3:34])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 224627162-[4-(2-Aminoethyl)phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

Product 1

HCID 21182945HCID 21182945, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-(2-aminoethyl)phenyl]benzo[b]thiophene (75 mg) was dissolved in dichloromethane (3.0 mL), treated with trimethylacetaldehyde (30 μL) and sodium triacetoxyborohydride (56 mg) sequentially and allowed to stir at ambient temperature for 3 h. The reaction mixture was concentrated, and column chromatography with ET3N:EtOAc (0-5%) afforded the product (55 mg).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-853b296d8f834d449f42658e467d5f4e
Source dataset
uspto-grants-2000_02
Patent number
US06025382

Linked notes

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