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

반응식

HRID 471097 반응식
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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-776d99c7e43f4cff8de80b160b98d4ac
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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