Triethylamine → (S)-4-[2-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

HRID 655548노트

반응식

HRID 655548 반응식
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]=O)[CH2:14][O:13][C:12]1([CH3:20])[CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:22]1[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][C@H:25]2[OH:30])[CH2:23]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH2:17][N:27]2[CH2:28][CH2:29][C:24]3([CH2:22][CH2:23]3)[C@H:25]([OH:30])[CH2:26]2)[CH2:14][O:13][C:12]1([CH3:20])[CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride2회HCID 60018412(S)-2,2-Dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

생성물 1

HCID 67080106(S)-4-[2-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester수율 97.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (8.51 g, 30.7 mmol) in dichloromethane (140 mL) were added (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2; 5.03 g, 30.7 mmol), triethylamine (3.11 g, 30.7 mmol) and sodium triacetoxyborohydride (9.11 g, 43.0 mmol) at room temperature. After 1 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane. The aqueous layer was extracted twice with dichloromethane, the combined organic phases were dried (MgSO4), filtered, and evaporated to afford the title compound (11.6 g, 97%). Light yellow gum, MS (ISP)=389.3 (M+H)+.

후처리

  1. customAfter 1 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-02fe066b98094a538eb5ff5f7943d634
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071586B2

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