Di-tert-butyl dicarbonate → Tert-butyl{2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropyl}carbamate

HRID 2194922노트

반응식

HRID 2194922 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[C:19]#[N:20])=[C:14]([CH3:28])[CH:13]=1.[O:29](C(OC(C)(C)C)=O)[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=O.[BH4-].[Na+]>CCO.C1COCC1>[C:33]([O:32][C:30](=[O:29])[NH:20][CH2:19][CH:18]([C:15]1[CH:16]=[CH:17][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:13][C:14]=1[CH3:28])[CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([CH3:36])([CH3:35])[CH3:34]

참가 물질

5

반응물 3

HCID 90495Di-tert-butyl dicarbonateHCID 4311764Sodium borohydrideHCID 674474272-[2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropanenitrile

생성물 1

HCID 131730115Tert-butyl{2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropyl}carbamate

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

To a solution of 2-[2′-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropanenitrile from step 2 (1 eq.) in EtOH/THF (3:1; 0.1M) at room temperature was added cobaltous chloride hexahydrate (CoCl2.6H2O; 2 eq.), followed by (BOC)2O (2 eq.) and finally sodium borohydride (10 eq.) portionwise. The final black mixture was stirred for 3 h at room temperature, quenched with HCl (1N). The pH was adjusted to 8 using saturated aqueous Na2CO3 and the resulting mixture was extracted several times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 75% in 30 min) afforded the desired compound as a colorless oil.

후처리

  1. customquenched with HCl (1N)
  2. extractionthe resulting mixture was extracted several times with EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  7. washeluting with Hex/EtOAc (10 to 75% in 30 min)

출처 및 근거

ORD 기록
ord-286d156192604ba6ae476c5bd7f162ee
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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