Tert-butyl 4-cyanophenylcarbamate → Tert-butyl N-(4-(aminomethyl)phenyl)carbamate

HRID 1191033

반응식

HRID 1191033 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.C(O)(C)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 10130644Tert-butyl 4-cyanophenylcarbamate

생성물 1

HCID 2794659Tert-butyl N-(4-(aminomethyl)phenyl)carbamate수율 36%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 22597222Tetrahydrofuran 2-propanol용매

실험 절차

Add a solution of 4-(tert-butoxycarbonylamino)-benzonitrile (1 g, 4.58 mmol) in THF/iso-propanol (1:1, 142 mL) to 10% Pd/C (Degussa type E101, 0.56 g, 0.26 mmol) via syringe under N2. Purge the reaction mixture with nitrogen and submit the mixture to hydrogenation at 50 psi overnight. Filter the catalyst through Celite® and wash thoroughly with iso-propanol (100 mL) and THF (100 mL). Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with DCM/2M ammonia in methanol (1:0 to 95:5 gradient over 30 min; 95:5 over 3 min; 95:5 to 9:1 gradient over 30 min and 9:1 over 30 min) to obtain the desired intermediate (0.364 g, 36%). MS (ES−) m/z: 220.1 (M−2H)−.

후처리

  1. customPurge the reaction mixture with nitrogen
  2. customat 50 psi overnight
  3. filtrationFilter the catalyst through Celite®
  4. washwash thoroughly with iso-propanol (100 mL) and THF (100 mL)
  5. concentrationConcentrate in vacuo
  6. custompurify the crude mixture by chromatography on silica gel eluting with DCM/2M ammonia in methanol (1:0 to 95:5 gradient over 30 min; 95:5 over 3 min; 95:5 to 9:1 gradient over 30 min and 9:1 over 30 min)

출처 및 근거

ORD 기록
ord-b422fa9a063a46dda99a9947d3e0f552
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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