Triethylamine → HCID 18319637, compound

HRID 1699376Notes

Reaction equation

HRID 1699376 reaction equation
[C:1]([C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(O)=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O>O1CCCC1>[OH:2][CH2:1][C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 18319626HCID 18319626, compound

Product 1

HCID 18319637HCID 18319637, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 9-carboxy-2,3-dihydro-1-benzoxepin-4-carboxylate (0.52 g) and triethylamine (0.33 ml) in tetrahydrofuran (5.2 ml) was added dropwise isobutyl chloroformate (0.31 ml) below 5° C. under ice-sodium chloride cooling. The reaction mixture was stirred for 30 minutes at the same temperature. The resulting precipitate was filtered off and washed with cold tetrahydrofuran. The filtrate was added to a solution of sodium borohydride (75 mg) in aqueous tetrahydrofuran (10 ml, 90% v/v) at 0° C. The reaction mixture was stirred for 30 minutes at the ambient temperature and evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:9) to give a solid of ethyl 2,3-dihydro-9-hydroxymethyl-1-benzoxepin-4-carboxylate (0.37 g).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with cold tetrahydrofuran
  3. additionThe filtrate was added to a solution of sodium borohydride (75 mg) in aqueous tetrahydrofuran (10 ml, 90% v/v) at 0° C
  4. stirringThe reaction mixture was stirred for 30 minutes at the ambient temperature
  5. customevaporated in vacuo
  6. customThe residue was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by medium pressure liquid chromatography (silica gel)
  11. additiona mixture of ethyl acetate and n-hexane (1:9)

Sources & evidence

ORD record
ord-aa5769da99224e4d8974f549c8ecff64
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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