HCID 86663718, 화합물 → Ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

HRID 579514

반응식

HRID 579514 반응식
[BH3:1].[OH:2][C:3]([C:6]([OH:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[C:10]([O:13][CH2:14][C:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH2:21][CH2:22][CH:23]=[CH2:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:12])[CH3:11]>ClCCl.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir].C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:10]([O:13][CH2:14][C:15]([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])([CH2:21][CH2:22][CH2:23][CH2:24][B:1]1[O:9][C:6]([CH3:8])([CH3:7])[C:3]([CH3:5])([CH3:4])[O:2]1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:12])[CH3:11]

참가 물질

6

반응물 2

HCID 86663718HCID 86663718, 화합물HCID 178419189HCID 178419189, 화합물

생성물 1

HCID 66832797Ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate수율 54%

시약·촉매·용매 3

HCID 742671,2-Bis(diphenylphosphino)ethane촉매HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimer촉매HCID 6344Dichloromethane용매2회

실험 절차

While under an argon atmosphere, a solution of chloro(1,5-cyclooctadiene)iridium(I) dimer (160 mg, 0.23 mmol) and 1,2-bis(diphenyl-phosphino) ethane (190 mg, 0.48 mmol) in dichloromethane (50 mL) was treated with pinacol borane (7.78 g, 61 mmol, 8.8 mL) and stirred for 15 minutes. To this mixture was added a solution of ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoate (10 g, 30.4 mmol) in dichloromethane (50 mL). After stirring for 19 h at room temperature the solution was concentrated and purified using a combiflash system (120 g column, eluting with 5-50% ethyl acetate in heptanes) to give ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (7.5 g, 54%). 1H NMR (CDCl3) δ 5.49 (bs, 1H), 4.72 (d, 1H), 4.33 (d, 1H), 4.23 (q, 2H), 2.18 (m, 1H), 2.01 (s, 3H), 1.69 (m, 2H), 1.43 (s, 9H), 1.29 (m, 4H), 1.23 (s, 12H), 0.88 (t, 3H), 0.74 (t, 2H). MS found for C22H40BNO8 m/z [480(M+Na)].

후처리

  1. stirringAfter stirring for 19 h at room temperature the solution
  2. concentrationwas concentrated
  3. custompurified
  4. washa combiflash system (120 g column, eluting with 5-50% ethyl acetate in heptanes)

출처 및 근거

ORD 기록
ord-7a260365f3ba4007bc5b2e4979529296
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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