Sodium Sulfate → Phenylmethyl ({(3S)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-3-pyrrolidinyl}methyl)carbamate

HRID 657058노트

반응식

HRID 657058 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=O)=[CH:4][CH:3]=1.[NH:16]1[CH2:20][CH2:19][C@@H:18]([CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17]1.NC[C@H]1CCN(C(OC(C)(C)C)=O)C1.[O-]S([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH2:13][N:16]2[CH2:20][CH2:19][C@@H:18]([CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:17]2)=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 24436Sodium SulfateHCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 45072660benzyl ((R)-pyrrolidin-3-yl)methylcarbamateHCID 86635311(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde

생성물 1

HCID 86635345Phenylmethyl ({(3S)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-3-pyrrolidinyl}methyl)carbamate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (7-fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde (1.17 g, 5.71 mmol) and phenylmethyl [(3R)-3-pyrrolidinylmethyl]carbamate (may be prepared analogously to the 3R isomer of Preparation 23(b) in WO2006002047, from (R)-3-(aminomethyl)-1-N-Boc-pyrrolidine) (1.34 g, 5.71 mmol) in 1:1 CH2Cl2:MeOH (80 mL) were added 8 eq. Na2SO4 (6.5 g, 46 mmol) and the reaction was stirred at ambient temperature for 18 h. The intermediate imine was treated with sodium triacetoxyborohydride (3.63 g, 17.0 mmol) and stirred for an additional 16 h. The solvents were removed under reduced pressure; the residue was partitioned between ethyl acetate and aqueous saturated NaHCO3, and the organic layer was dried over Na2SO4. Purification by column chromatography on silica gel, (1% to 20% methanol:dichloromethane gradient) yielded a light amber oil. (820 mg, 34%).

후처리

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and aqueous saturated NaHCO3
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customPurification by column chromatography on silica gel, (1% to 20% methanol:dichloromethane gradient)
  5. customyielded a light amber oil

출처 및 근거

ORD 기록
ord-9f35f219001b4e57aaf4d9cccf6c5107
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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