Sodium borohydride → [2-Amino-1-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-methyl-2-phenylethyl]dimethylamine

HRID 20825

反応式

HRID 20825 の反応式
[CH3:1][N:2]([CH3:16])[C:3]([CH3:15])([CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[C:4]#[N:5].[C:17]1([Li])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C(OCCCC)CCC.C1COCC1.CO>[NH2:5][CH:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([N:2]([CH3:16])[CH3:1])([CH2:6][O:7][Si:8]([C:11]([CH3:12])([CH3:14])[CH3:13])([CH3:10])[CH3:9])[CH3:15]

参加物

8

反応物 4

HCID 4311764Sodium borohydrideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 86624947HCID 86624947、化合物HCID 178506676HCID 178506676、化合物

生成物 1

HCID 68562132[2-Amino-1-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-methyl-2-phenylethyl]dimethylamine収率 33%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8909Butyl ether溶媒

実験手順

The title compound (930 mg, 33%) was prepared from 2-(dimethylamino)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methylpropanenitrile D47 (2.1 g, 8.67 mmol), phenyl lithium (10.0 ml of a 1.8M solution in dibutyl ether, 18.0 mmol) in THF (30 ml) followed by sodium borohydride (830 mg, 26.0 mmol) in methanol (50 ml) in a similar manner to that described in D2. Chromatography (Biotage Horizon) to isolate the title compound was carried out using (i) 0 to 100% ethyl acetate/pentane, (ii) 100% ethyl acetate and (iii) 0 to 20% methanol/ethyl acetate. The product containing fractions were combined and evaporated. Mass spectrum (Electrospray LC/MS), API+: Found 323 (MH+), 306 (M−16). C18H34N2OSi requires 322. Ret. time 2.35-2.39 min. (broad peak).

後処理

  1. customChromatography (Biotage Horizon) to isolate the title compound

出典と根拠

ORDレコード
ord-ab8fe43283da461ba326272650a1c314
出典データセット
uspto-grants-2010_06
特許番号
US07745642B2

関連ノート

読み込み中…