N-bromobutanimide → (3R,8aR)-3-Bromomethyl-3-methyltetrahydropyrrolo[2,1-c][1,4]oxazine-1,4-dione

HRID 133735

반응식

HRID 133735 반응식
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10](=[CH2:21])[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[C:18]([OH:20])=[O:19])=[O:12]>CN(C=O)C>[Br:8][CH2:21][C@:10]1([CH3:9])[O:19][C:18](=[O:20])[C@H:14]2[CH2:15][CH2:16][CH2:17][N:13]2[C:11]1=[O:12]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 11615290(2R)-1-Methacryloylpyrrolidin-2-carboxylic Acid

생성물 1

HCID 11615879(3R,8aR)-3-Bromomethyl-3-methyltetrahydropyrrolo[2,1-c][1,4]oxazine-1,4-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

NBS (16 g, 89.9 mmol) was dissolved in DMF (50 ml) and added at room temperature to a solution of (2R)-1-(2-methylacryloyl)pyrrolidine-2-carboxylic acid (11.5 g, contains 8.0 g of the corresponding starting material, 43.4 mmol) in DMF (50 ml). The mixture was stirred for 20 h and evaporated at 80-90° C. The residue was mixed with water (250 ml) and extracted with ethyl acetate (4×80 ml). The combined ethyl acetate phases were washed with 1 M NaHCO3 solution (2×50 ml) and water (1×50 ml). The organic phase was dried over Na2SO4 and evaporated. The yield of the crude oil was 9.3 g. Ethyl acetate (10 ml) was added and the mixture was stirred in an ice bath. The precipitated product was filtered and washed with cooled ethyl acetate. The yield was 1.2 g. 1H NMR (DMSO-d6): 1.58 (3H, s), 1.75-2.10 (3H, m), 2.25 (1H, m), 3.30-3.55 (2H, m), 3.87 (1H, d, J=11.4 Hz), 4.03 (1H, d, J=11.4 Hz), 4.70 (1H, m).

후처리

  1. customevaporated at 80-90° C
  2. additionThe residue was mixed with water (250 ml)
  3. extractionextracted with ethyl acetate (4×80 ml)
  4. washThe combined ethyl acetate phases were washed with 1 M NaHCO3 solution (2×50 ml) and water (1×50 ml)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated
  7. additionEthyl acetate (10 ml) was added
  8. stirringthe mixture was stirred in an ice bath
  9. filtrationThe precipitated product was filtered
  10. washwashed with cooled ethyl acetate

출처 및 근거

ORD 기록
ord-a3a42a8401b34b999aa18c3e4a81b737
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390923B2

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