Methanol → 3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

HRID 5407

Reaction equation

[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([C:19](OCC)=[O:20])[NH:11][C:10]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO>C(O)(C)(C)C>[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([CH2:19][OH:20])[NH:11][C:10]1=[O:24])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 55 °C

Procedure

The major isomer of ethyl 3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane-10-carboxylate (0.68 g, 2.0 mmol) is dissolved in t-butanol (10 mL). Sodium borohydride (0.23 g, 6.0 mmol) is added and the reaction is warmed to 55° C. Methanol (2.0 mL) is added over a twenty minute period, and the reaction is kept at 55° C. for an additional 1 hour. The reaction is then partitioned between ethyl acetate and water, and the aqueous phase is extracted several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (50% ethyl acetate/hexane) to give 3-t-butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane, MS: M+1=300.

Workup

customThe reaction is then partitioned between ethyl acetate and water
extractionthe aqueous phase is extracted several times with ethyl acetate
dry with materialThe combined organic layers are dried (MgSO4)
customthe solvent is evaporated
customThe crude product is purified by silica gel chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-429516784f194c80be8e088df5ef86d4
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244889

Linked notes

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