Sodium triacetoxyborohydride → 1-(9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone

HRID 471069

反応式

HRID 471069 の反応式
FC(F)(F)C(O)=O.[F:8][C:9]([F:24])([F:23])[C:10]([N:12]1[CH2:17][C:16]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:15][CH2:14][CH2:13]1)=[O:11].[Si:25]([O:32][CH2:33][CH2:34][C:35]1[CH:36]=[C:37]([CH:40]=O)[S:38][CH:39]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[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:25]([O:32][CH2:33][CH2:34][C:35]1[CH:36]=[C:37]([CH2:40][N:20]2[CH2:21][CH2:22][C:16]3([O:15][CH2:14][CH2:13][N:12]([C:10](=[O:11])[C:9]([F:8])([F:23])[F:24])[CH2:17]3)[CH2:18][CH2:19]2)[S:38][CH:39]=1)([C:28]([CH3:29])([CH3:31])[CH3:30])([CH3:27])[CH3:26]

参加物

8

反応物 4

HCID 5049666Sodium triacetoxyborohydrideHCID 579889073-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehydeHCID 579891104-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehydeHCID 866367502,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

生成物 1

HCID 579892241-(9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

2,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate (example 12, step d) (1.084 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) (1.0 g), and AcOH (0.16 mL) in N-methyl-2-pyrrolidinone (15 mL). After 5 min, sodium triacetoxyborohydride (1.57 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 ethyl acetate:isohexane:triethylamine, 1:20:1 separated the two isomeric products and gave the subtitled compound as an oil. Yield 1.04 g.

後処理

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed three times with water
  3. customevaporated in vacuo
  4. customPurification by silica gel chromatography
  5. washeluting with ethyl acetate
  6. customisohexane:triethylamine, 1:20:1 separated the two isomeric products

出典と根拠

ORDレコード
ord-efde6bf7cc3344aeaf845b5089f0d163
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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