Chloroform → 3-Phenylazetidine

HRID 1916251Notes

Reaction equation

HRID 1916251 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9]2)C=CC=CC=1.C(Cl)(Cl)Cl.[OH-].[NH4+]>CO>[C:12]1([CH:10]2[CH2:11][NH:8][CH2:9]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14923Ammonium HydroxideHCID 160894471-(Diphenylmethyl)-3-phenylazetidine

Product 1

HCID 289015863-Phenylazetidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound C43 was prepared according to the general procedure for the synthesis of C40 in Example 9, except that 1-(diphenylmethyl)-3-phenylazetidine (See M. C. Hillier & C-y. Chen, J. Organic Chem. 2006, 71, 7885-7887) was used instead of 1-(diphenylmethyl)-3-(4-fluorophenoxy)azetidine, and the silica gel chromatography was carried out with 100:5:1 chloroform:MeOH:concentrated aqueous ammonium hydroxide as eluant. Yield: 427 mg (contains some impurities), <3.21 mmol, <19%. LCMS m/z 134.0 (M+1). 1H NMR (400 MHz, CD3OD), product peaks only: δ 4.02 (m, 2H), 4.11 (m, 3H), 7.29 (m, 5H).

Workup

  1. customCompound C43 was prepared

Sources & evidence

ORD record
ord-562e02343469470b8af34a5edcd55510
Source dataset
uspto-grants-2013_12
Patent number
US08618117B2

Reaction notes

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