Sodium triacetoxyborohydride → (9-(2-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 470967노트

반응식

HRID 470967 반응식
FC(F)(F)C(O)=O.[CH3:8][C:9]1[S:10][CH:11]=[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])[N:13]=1.[Si:27]([O:34][CH2:35][CH2:36][C:37]1[S:41][C:40]([CH2:42][CH:43]=O)=[CH:39][CH:38]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[Si:27]([O:34][CH2:35][CH2:36][C:37]1[S:41][C:40]([CH2:42][CH2:43][N:24]2[CH2:25][CH2:26][C:20]3([O:19][CH2:18][CH2:17][N:16]([C:14]([C:12]4[N:13]=[C:9]([CH3:8])[S:10][CH:11]=4)=[O:15])[CH2:21]3)[CH2:22][CH2:23]2)=[CH:39][CH:38]=1)([C:30]([CH3:31])([CH3:33])[CH3:32])([CH3:29])[CH3:28]

참가 물질

6

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 579888962-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetaldehydeHCID 66964121(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

생성물 1

HCID 57989154(9-(2-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

시약·촉매·용매 2

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

실험 절차

(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 4, step h) (0.25 g) was added to a solution of 2-(5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetaldehyde (0.2 g) (example 4, step g) in a mixture of NMP (5 mL) and acetic acid (0.04 mL). The resulting mixture was stirred for 5 min then sodium triacetoxyborohydride (0.22 g) was added. The mixture was stirred for 1 h and poured into pH 7.2 buffer (50 mL). The aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organics were washed with pH 7.2 buffer (50 mL) and brine (50 mL), then dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 4:1:0.05 isohexane:ethyl acetate:triethylamine to 95:5 ethyl acetate:triethylamine to give the subtitled compound as a yellow oil. Yield 0.23 g.

후처리

  1. stirringThe mixture was stirred for 1 h
  2. additionpoured into pH 7.2 buffer (50 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organics were washed with pH 7.2 buffer (50 mL) and brine (50 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification
  9. washeluting with 4:1:0.05 isohexane

출처 및 근거

ORD 기록
ord-71b15c90daf4401c90f7ada1ca88d1a0
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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