HCID 18986940, compound → HCID 18986947, compound

HRID 2397073Notes

Reaction equation

HRID 2397073 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([NH:16][CH2:17][C:18](O)=[O:19])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:16][CH2:17][CH2:18][OH:19].[CH:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH2:6][C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 18986940HCID 18986940, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18986947HCID 18986947, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-H-Dibenzo[a,d]cyclohepten-5-ylglycine (4.8g, Example 1c) was added in portions to a solution of lithium aluminium hydride (54ml of 1.0M solution) in 30ml dry THF at 0° C. The reaction was allowed to stand at room temperature overnight, quenched with 2N sodium hydroxide and poured through Celite. The filtrate was washed with water, dried over MgSO4 and solvent removed in vacuo to leave a residue which was induced to crystallised in ethyl acetate or dichloromethane to give 5H-dibenzo[a,d]cycloheptene glycinol. 1H NMR (360MHz, d4MeOH) δ 3.05-3.17 (2H, m), 3.29-3.33 (1H, m), 3.89-3.94 (1H, m), 6.90-6.97 (2H, m), 7.23-7.38 (8H, m).

Workup

  1. customquenched with 2N sodium hydroxide
  2. additionpoured through Celite
  3. washThe filtrate was washed with water
  4. dry with materialdried over MgSO4 and solvent
  5. customremoved in vacuo
  6. customto leave a residue which
  7. customto crystallised in ethyl acetate

Sources & evidence

ORD record
ord-19cb4894e1824908a513ccd264f24492
Source dataset
uspto-grants-1996_02
Patent number
US05495047

Reaction notes

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