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

HRID 471097

反応式

HRID 471097 の反応式
FC(F)(F)C(O)=O.[F:8][C:9]1([F:30])[CH2:14][N:13]([C:15]([C:17]2[N:18]=[C:19]([CH:22]([CH3:24])[CH3:23])[S:20][CH:21]=2)=[O:16])[CH2:12][C:11]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[O:10]1.[Si:31]([O:38][CH2:39][CH2:40][C:41]1[CH:42]=[C:43]([CH:46]=O)[S:44][CH:45]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].[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:31]([O:38][CH2:39][CH2:40][C:41]1[CH:42]=[C:43]([CH2:46][N:27]2[CH2:28][CH2:29][C:11]3([O:10][C:9]([F:8])([F:30])[CH2:14][N:13]([C:15]([C:17]4[N:18]=[C:19]([CH:22]([CH3:24])[CH3:23])[S:20][CH:21]=4)=[O:16])[CH2:12]3)[CH2:25][CH2:26]2)[S:44][CH:45]=1)([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:33])[CH3:32]

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 67292751(2,2-Difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone trifluoroacetate

生成物 1

HCID 57989002(9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-2,2-difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

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-Difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone trifluoroacetate (example 44, step b) (0.40 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) (0.36 g) and AcOH (0.05 mL) in N-methyl-2-pyrrolidinone (5 mL). After 5 min, sodium triacetoxyborohydride (0.28 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 0.24 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 20:80:5 ethyl acetate
  6. customisohexane:triethylamine separated the two isomeric products

出典と根拠

ORDレコード
ord-776d99c7e43f4cff8de80b160b98d4ac
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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