tert-Butyl methyl ether → HCID 68499756, compound

HRID 1176596Notes

Reaction equation

[O:1]=[C:2]1[N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:7]2[C:17]([C:21](OC)=[O:22])=[CH:18][CH:19]=[CH:20][C:6]=2[CH2:5][CH2:4][CH2:3]1.[BH4-].[Li+].C(=O)([O-])O.[Na+].COC(C)(C)C>O1CCCC1>[OH:22][CH2:21][C:17]1[C:7]2[N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]=2[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1.500 g of methyl 2-oxo-1-(trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate in 35 ml of tetrahydrofuran is admixed with 0.205 g of lithium borohydride. The reaction mixture is stirred at 50° C. over 4 hours and subsequently poured onto 300 ml of a 1:1 mixture of saturated aqueous sodium hydrogencarbonate solution and tert-butyl methyl ether. The phases are separated and the aqueous phase is extracted with 150 ml of tert-butyl methyl ether. The combined organic phases are washed with 150 ml of water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (1:1 EtOAc-heptane); Rt=4.38.

Workup

customThe phases are separated
extractionthe aqueous phase is extracted with 150 ml of tert-butyl methyl ether
washThe combined organic phases are washed with 150 ml of water
dry with materialdried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-c0001a16f94f4e61b41b3097a53ad93b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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