Boron tribromide → HCID 10425271, compound

HRID 1975076Notes

Reaction equation

HRID 1975076 reaction equation
B(Br)(Br)Br.C([O:12][C@@H:13]1[C:18]([CH3:20])([CH3:19])[O:17][C:16]2[CH:21]=[C:22]([C:24]#[N:25])[S:23][C:15]=2[C@H:14]1[N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=[O:32])C1C=CC=CC=1>ClCCl>[C:24]([C:22]1[S:23][C:15]2[C@@H:14]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]3=[O:32])[C@H:13]([OH:12])[C:18]([CH3:20])([CH3:19])[O:17][C:16]=2[CH:21]=1)#[N:25]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10386064HCID 10386064, compound

Product 1

HCID 10425271HCID 10425271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.0 M in dichloromethane, 17.6 mL, 17.6 mmol) was slowly added to a solution of trans-6-benzyloxy-2-cyano-5,6-dihydro-5,5-dimethyl-7-(2-oxopiperidin-1-yl) -7H-thieno[3,2-b]pyran (1.4 g, 3.5 mmol) in dichloromethane (40 mL) at0° C. and stirred for 1h. The solution was poured into ice water. The organic layer was washed with water and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography using 3% methanol in dichloromethane as the eluant. The product was recrystallized from dichloromethane/hexanes to give a colorless solid, 0.997 g (93%); mp 212°-214° C.; IR(KBr): 2210, 1624, 1558 and 1486 cm-1 ; MS: m/z 307 (MH+); 1H NMR(CDCl3): δ 1.29 (s, 3H), 1.50 (s, 3H), 1.77-1.90 (m, 4H), 2.53 (m, 2H), 3.17 (m, 2H), 3.66 (d, J=5.9 Hz, 1H), 3.80 (dd, J=5.9 Hz, J=9.4 Hz, 1H), 5.85 (d, J=9.4 Hz, 1H), 5.92 (bs, 1H) and 7.07 (s, 1H).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by flash chromatography
  5. customThe product was recrystallized from dichloromethane/hexanes
  6. customto give a colorless solid, 0.997 g (93%)

Sources & evidence

ORD record
ord-6ad3dbb4d0b248198197627e24c2a722
Source dataset
uspto-grants-1994_02
Patent number
US05284857

Reaction notes

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