m-Chloroperbenzoic acid → 6-Benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline 1-oxide

HRID 1765328Notes

Reaction equation

HRID 1765328 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:21][CH2:20][C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:27]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:21][CH2:20][C:19]2[N+:18]([O-:27])=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 211070726-Benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline

Product 1

HCID 211070716-Benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline 1-oxideYield 66.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline (1.66 g, 5.87 mmol) in chloroform (13 mL) at 0° C. under nitrogen was added 3-chloroperoxybenzoic acid (1.06 g net, 6.16 mmol). The reaction mixture was then slowly warmed to room temperature. After 1 d, the reaction mixture was chromatographed on basic alumina (eluted with a 0–3% step-wise gradient of methanol in methylene chloride). The title compound (1.16 g, 66.5%) was obtained as a light yellow solid. 13C NMR (400 MHz, CDCl3) δ 155.7, 147.2, 137.3, 136.3, 133.5, 128.5, 128.1, 128.0, 126.5, 122.6, 66.8, 45.4, 36.7, 27.3, 22.9. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=6.2 Hz, 1H), 7.31 (m, 5H), 7.00 (m, 2H), 5.07 (s, 2H), 3.98 (br s, 1H), 3.12 (m, 2H), 2.95 (m, 1H), 2.70 (dd, J=7.9, 16.0 Hz, 1H), 2.11 (m, 1H), 1.86 (br s, 1H). HPLC/MS [M+H]+, 299.

Workup

  1. customthe reaction mixture was chromatographed on basic alumina (
  2. washeluted with a 0–3% step-wise gradient of methanol in methylene chloride)

Sources & evidence

ORD record
ord-cfa98f3144bb4aa9b88d5c7ce117ec7a
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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