Tetrahydrofuran → (S)-3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methylpropylmethyl carbamate

HRID 370214

반응식

HRID 370214 반응식
[F:1][C:2]1[CH:29]=[CH:28][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16]N4C(O)C5C(=CC=CC=5)C4=O)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C[N:31]=[C:32]=[O:33].[C:34]([O-])([O-])=O.[K+].[K+].C1C[O:43][CH2:42][CH2:41]1>>[C:32](=[O:33])([O:43][CH2:42][CH2:41][C@H:16]([CH3:34])[CH2:15][N:12]1[CH2:11][CH2:10][CH:9]([C:6]2[C:5]3[CH:28]=[CH:29][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:14][CH2:13]1)[NH2:31]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 184672142-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl-2,3-dihydro-3-hydroxy-1H-isoindol-1-one

생성물 1

HCID 53784931(S)-3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methylpropylmethyl carbamate수율 73%

실험 절차

To a solution of 2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2,3-dihydro-3-hydroxy-1H-isoindol-1-one (3.1 g, 10.6 mmol) in dry THF (120 ml) was added methyl isocyanate (0.66 ml, 11.1 mmol) followed by milled K2CO3 (2.2 g, 15.9 mmol) at room temperature, under nitrogen. The reaction mixture was stirred for 3 days at which time it was filtered through a pad of Celite and the solids washed with EtOAc. The combined filtrates were concentrated to give the crude product which was purified via flash column chromatography (silica gel, 2% Et3N/EtOAc). The product containing fractions were concentrated to give 2.7 g (73%) of the desired product as an oil which solidified on standing. Recrystallization from EtOAc/pet.ether gave the product as a solid, m.p.=72-74° C.

후처리

  1. filtrationwas filtered through a pad of Celite
  2. washthe solids washed with EtOAc
  3. concentrationThe combined filtrates were concentrated
  4. customto give the crude product which
  5. customwas purified via flash column chromatography (silica gel, 2% Et3N/EtOAc)
  6. additionThe product containing fractions
  7. concentrationwere concentrated

출처 및 근거

ORD 기록
ord-15401bbb1a3d438aa3c006c3f058b3d7
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140345

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