反応式
FC(F)(F)C(O)=O.[CH3:8][C:9]1[S:13][C:12]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])=[CH:11][CH:10]=1.[Si:27]([O:34][CH2:35][CH2:36][C:37]1[CH:38]=[C:39]([CH:42]=O)[S:40][CH:41]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].[Si](OCCC1C=CSC=1C=O)(C(C)(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O.O.CC(O)=O>[Si:27]([O:34][CH2:35][CH2:36][C:37]1[CH:38]=[C:39]([CH2:42][N:24]2[CH2:25][CH2:26][C:20]3([O:19][CH2:18][CH2:17][N:16]([C:14]([C:12]4[S:13][C:9]([CH3:8])=[CH:10][CH:11]=4)=[O:15])[CH2:21]3)[CH2:22][CH2:23]2)[S:40][CH:41]=1)([C:30]([CH3:31])([CH3:33])[CH3:32])([CH3:29])[CH3:28]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
実験手順
(5-Methylthiophen-2-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 9, step b) (0.230 g) was added to a stirred solution of a 4:1 mixture of 4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehyde and 3-(2-(tert-butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehyde (example 27, step b) (0.20 g) and AcOH (0.033 mL) in N-methyl-2-pyrrolidinone (3 mL). After 5 min, sodium triacetoxyborohydride (0.35 g) was added. After 16 h water was added and the mixture extracted with ethyl acetate. The ethyl acetate layer was washed three times with water and evaporated in vacuo. Purification by silica gel chromatography eluting with 20:80:5 ethyl acetate:isohexane:triethylamine, separated the two isomeric products and gave the subtitled compound as a gum. Yield 0.21 g.
後処理
- extractionthe mixture extracted with ethyl acetate
- washThe ethyl acetate layer was washed three times with water
- customevaporated in vacuo
- customPurification by silica gel chromatography
- washeluting with 20:80:5 ethyl acetate
- customisohexane:triethylamine, separated the two isomeric products
出典と根拠
- ORDレコード
- ord-70db08011b034097b8b32817ddbc77a0
- 出典データセット
- uspto-grants-2014_01
- 特許番号
- US08629271B2
関連ノート
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