Sodium triacetoxyborohydride → HCID 11352263, compound

HRID 479361Notes

Reaction equation

HRID 479361 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.[C:17]([O:21][C:22]([N:24]1[CH2:30][CH2:29][C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH2:34][CH:35]=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:17]([O:21][C:22]([N:24]1[CH2:30][CH2:29][C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH2:34][CH2:35][N:13]([CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)[CH2:14][CH2:15][CH3:16])[CH2:26][CH2:25]1)=[O:23])([CH3:18])([CH3:19])[CH3:20]

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 100821727-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amineHCID 113121495-Oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 11352263HCID 11352263, compound

Procedure

To a solution of (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine prepared as described in Example 1 (800 mg, 3.3 mmol, 1 eq) in 1,2-dichlororethane (40 mL) under inert atmosphere was added 5-oxo-4-(4-oxo-butyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.0 g, 3.6 mmol, 1.1 eq.) in a single portion followed by the sodium triacetoxyborohydride (1.7 g, 8.25 mmol, 2.5 eq.). The reaction was stirred at room temperature for 20 hr, concentrated in-vacuo and then partitioned between 10% KOH (50 mL) and ethyl acetate (100 mL). The organic layer was washed with brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography gave 1.1 g of 4-{4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-5 -oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationconcentrated in-vacuo
  2. custompartitioned between 10% KOH (50 mL) and ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-c7b7b0598ba04c7896e8cc20547e3201
Source dataset
uspto-grants-2003_11
Patent number
US06645958B2

Reaction notes

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