Tert-butyl 6-(1-hydroxyethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate → Tert-butyl 6-acetyl-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

HRID 32115Notes

Reaction equation

HRID 32115 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]([OH:20])[CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18](=[O:20])[CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68681678Tert-butyl 6-(1-hydroxyethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Product 1

HCID 68680146Tert-butyl 6-acetyl-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [6-(1-hydroxy-ethyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-carbamic acid tert-butyl ester (2.63 g, 9.04 mmol, 1.0 eq) and MnO2 (Aldrich, 10.2 g, 117.5 mmol, 13 eq) in CH2Cl2 (100 mL) was stirred at RT overnight. The mixture was passed through a pad of Celite® and the pad was washed with CH2Cl2 (100 mL×2). The concentration of the filtrate afforded the title compound as a white sticky semi-solid. MS (ESI, pos. ion) m/z: 290 (M+1).

Workup

  1. washthe pad was washed with CH2Cl2 (100 mL×2)

Sources & evidence

ORD record
ord-3d1003c0a84d492c88bf3858ba854fe9
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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