Tetrahydrofuran → HCID 22905385, compound

HRID 1376646Notes

Reaction equation

HRID 1376646 reaction equation
[CH2:1]([N:4]1[CH2:10][CH:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][C:7]2[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:6]=2[C:5]1=[O:23])[CH:2]=[CH2:3].C12BC(CCC1)CCC2.C1C[O:36]CC1>>[OH:36][CH2:3][CH2:2][CH2:1][N:4]1[CH2:10][CH:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][C:7]2[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:6]=2[C:5]1=[O:23]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 22905239HCID 22905239, compound

Product 1

HCID 22905385HCID 22905385, compoundYield 77%

Procedure

To a magnetically stirred solution of 2-allyl-4-benzyl-8-iodo-2,3,4,5-tetrahydro-1H-5-oxa-2-benzazepin-1-one (0.9234 grams, 2.2 mmol) in 4 mL THF at room temperature under an atmosphere of nitrogen was added 6.0 mL of a 0.5M solution of 9-borabicylo[3.3.1]nonane in THF (3 mmol) and the mixture stirred for 1 hour. The reaction was quenched with 6 mL of a solution of 2 grams of sodium hydroxide and 22 mL of a 1:1 mixture of ethanol and water. To the resulting solution was added 7 mL of a 30% solution hydrogen peroxide in water. After 30 minutes the mixture was partitioned between diethyl ether and water. The organic layer was washed with 10% citric acid and brine, dried over sodium sulfate, concentrated in vacuo, and purified by column chromatography (SiO2, using 1:5 ethyl acetate/methylene chloride as the eluting solvent, Rf (product)=0.22) to yield 0.74 grams (77%) of 2-(3-hydroxypropyl)-4-benzyl-8-iodo-2,3,4,5-tetrahydro-1H-5-oxa-2-benzazepin-1-one. 1H NMR (CDCl3, dTMS) 8.08 (1H, d, 4JHH =2 Hz, C9-H), 7.71 (1H, dd, 4JHH =2 Hz, 3JHH =8 Hz, C7-H), 7.4 -7.2 (5H, m, C6H5), 6.78 (1H, d, 3JHH =8 Hz, C6-H), 4.64 (1H, m, ArOCH), 3.70 (2H, m, CH2OH), 3.58 (2H, bt, 3JHH =5 Hz, NCH2CH2), 3.39 (1H, dd, 2JHH =15 Hz, 3JHH =8 Hz, C3-H), 3.24 (1H, dd, 2JHH =15 Hz, 3JHH =3 Hz, C3-H), 3.1 (1H, dd, 2JHH =14 Hz, 3JHH =7 Hz, CHHPh), 2.76 (1H, dd, 2JHH =14 Hz, 3JHH =7 Hz, CHHPh), 1.68 (2H, m, CH2CH2OH). 13C NMR (CDCl3) 168.3, 152.6, 141.6, 139.4, 136.2, 132.1, 131.9, 129.2, 129.0, 128.8, 128.4, 127.0, 124.7, 86.8, 85.7, 58.0, 49.9, 44.5, 38.8, 30.3. IR (NaCl, cm-1) 3422 (b), 1636, 1463, 1436, 1217, 1064.

Workup

  1. customThe reaction was quenched with 6 mL of a solution of 2 grams of sodium hydroxide and 22 mL of a 1:1 mixture of ethanol and water
  2. additionTo the resulting solution was added 7 mL of a 30% solution hydrogen peroxide in water
  3. customAfter 30 minutes the mixture was partitioned between diethyl ether and water
  4. washThe organic layer was washed with 10% citric acid and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (SiO2

Sources & evidence

ORD record
ord-df4c329a3345452b850cfd8dcc857566
Source dataset
uspto-grants-1997_09
Patent number
US05663166

Reaction notes

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