4-(Bromoacetyl)benzonitrile → (R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate

HRID 1948490노트

반응식

HRID 1948490 반응식
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4].[NH:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]1>C1(C)C=CC=CC=1>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([C:3](=[O:4])[CH2:2][N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]2)=[CH:6][CH:7]=1)#[N:10]

참가 물질

4

반응물 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 7161133ethyl 2-[(3R)-piperidin-3-yl]acetate

생성물 1

HCID 58374115(R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate수율 68.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of 4-(2-bromoacetyl)benzonitrile (5.5g, 24.55 mmol) in toluene was added (R)-ethyl 2-(piperidin-3-yl)acetate (4 g, 23.36 mmol). The reaction mixture was stirred for 4 days at room temperature and then stirred from one day at 50° C. Solvents were removed in vacuo. The resulting solids were triturated with EtOAc. The solid material was filtered and washed with EtOAc. The solid material was collected and dried to yield 5 g of (R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate. MS (M+1)=314. HPLC Peak RT=0.77 minutes.

후처리

  1. stirringstirred from one day at 50° C
  2. customSolvents were removed in vacuo
  3. customThe resulting solids were triturated with EtOAc
  4. filtrationThe solid material was filtered
  5. washwashed with EtOAc
  6. customThe solid material was collected
  7. customdried

출처 및 근거

ORD 기록
ord-8dce0bb7f8e54713a7240acfeed0ccf8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399451B2

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