(6-Hydroxymethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester → HCID 58841363, compound

HRID 32113Notes

Reaction equation

HRID 32113 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][OH: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:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58841393(6-Hydroxymethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester

Product 1

HCID 58841363HCID 58841363, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-hydroxymethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester (3.16 g, 11.4 mmol, 1.0 eq) and MnO2 (Aldrich, 12.9 g, 148.3 mmol, 13 eq) in CH2Cl2 (110 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: 298 (M+Na).

Workup

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

Sources & evidence

ORD record
ord-92bba4b588004ef48674d547f869dd0b
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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