1-(p-Chlorophenyl)cyclobutanecarboxylic acid → [1-(4-Chloro-phenyl)-cyclobutyl]-(3-hydroxymethyl-azepan-1-yl)-methanone

HRID 2110290Notes

Reaction equation

HRID 2110290 reaction equation
C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH:25]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]([CH2:32][OH:33])[CH2:26]1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2([C:45](O)=[O:46])[CH2:44][CH2:43][CH2:42]2)=[CH:37][CH:36]=1>C(Cl)Cl>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([C:41]2([C:45]([N:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]([CH2:32][OH:33])[CH2:26]3)=[O:46])[CH2:44][CH2:43][CH2:42]2)=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 2733179PyBroPHCID 21901984(Azepan-3-yl)methanol

Product 1

HCID 21902048[1-(4-Chloro-phenyl)-cyclobutyl]-(3-hydroxymethyl-azepan-1-yl)-methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tPrEtN (1.78 mL, 10.2 mmol) and pyBrOP (2.39 g, 5.12 mmol) were added at room temperature to a stirring solution of azepan-3-yl-methanol (0.4392 g, 3.41 mmol) and 1-(4-Chlorophenyl)-cyclobutanecarboxylic acid (1.0778 g, 5.12 mmol) in CH2Cl2 under N2. When the reaction was complete, the reaction was subjected to aqueous work-up. Silica gel purification (4:1 to 2:3 Hexanes: Ethyl acetate) provided the desired product in 95% yield (1.0395 g). LRMS: 321.91.

Workup

  1. customSilica gel purification (4:1 to 2:3 Hexanes: Ethyl acetate)

Sources & evidence

ORD record
ord-55d7f718f21645fcaa3fc0e865d476b1
Source dataset
uspto-grants-2009_04
Patent number
US07517892B2

Reaction notes

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