Diethyl Ether → tert-butyl N-{[1-(hydroxymethyl)cyclopentyl]methyl}carbamate

HRID 1817658Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([C:15](OC)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.CCOCC>C1COCC1.C(Cl)Cl>[OH:16][CH2:15][C:10]1([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of methyl 1-[(tert-butoxycarbonyl)amino]methylcyclopentanecarboxylate (1.50 g, 5.83 mmol) in THF (25.0 mL) at −78° C. was added dropwise 1.0 M diisobutylaluminum hydride in DCM (17.5 mL). The reaction was stirred for 2 hours with slow warming to −10° C. A saturated solution of K/Na tartrate was added, followed by ether. This mixture was stirred for 30 minutes at ambient temperature and the organic layer was separated and washed with water, and brine. The organic layer was then dried over sodium sulfate, and the solvent was removed in vacuo to afford the product (1.03 g, 77%). 1H NMR (300 MHz, CDCl3): δ 4.90 (br s, 1H), 3.27 (s, 2H), 3.06 (d, 2H), 1.5-1.17 (m, 8H), 1.44 (s, 9H).

Workup

stirringThis mixture was stirred for 30 minutes at ambient temperature
customthe organic layer was separated
washwashed with water, and brine
dry with materialThe organic layer was then dried over sodium sulfate
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-79bfcaea99c0434fa5be03c5c4133c75
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598257B2

Reaction notes

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