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

HRID 1501514Notes

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>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1([CH2:15][OH:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

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-f145277b7d1e46d8b373aed9c69409a4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206187B2

Reaction notes

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