Formaldehyde → HCID 68675855, compound

HRID 500450Notes

Reaction equation

HRID 500450 reaction equation
[ClH:1].[CH:2]1([C@H:8]2[N:13]3[CH:14]=[C:15]([C:20]([N:22]4[CH2:27][C@H:26]([CH3:28])[NH:25][C@H:24]([CH3:29])[CH2:23]4)=[O:21])[C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C=O.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[ClH:1].[CH:2]1([C@H:8]2[N:13]3[CH:14]=[C:15]([C:20]([N:22]4[CH2:23][C@H:24]([CH3:29])[N:25]([CH3:32])[C@H:26]([CH3:28])[CH2:27]4)=[O:21])[C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68674225HCID 68674225, compound

Product 1

HCID 68675855HCID 68675855, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-3-cyclohexyl-2,3-dihydro-6-[(cis)-3,5-dimethylpiperazin-1-yl-carbonyl]pyrrolo[1,2,3-de]-1,4-benzoxazine hydrochloride salt (100 mg, 0.26 mmol) in ethanol (10 ml) was added formaldehyde (37% in water; 1 ml, 12.5 mmol) and sodium triacetoxyborohydride (200 mg, 0.93 mmol). The mixture was stirred at room temperature for 30 minutes. The solvent was removed in vacuo. The residue was purified by flash chromatography eluting with 1-10% (v/v) methanol in dichloro-methane to afford the title compound as the free base. Hydrochloride salt formation was achieved by the addition of hydrogen chloride (2 M solution in diethyl ether; 2 ml) to the free base in dichloromethane (1 ml). The precipitate was filtered and dried to afford the title compound (1:1 hydrochloride salt). EsIMS: m/z=396.1 [M+H]+, 268; [α]D22−19.6° (c=2.1 mg/ml in methanol).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by flash chromatography
  3. washeluting with 1-10% (v/v) methanol in dichloro-methane

Sources & evidence

ORD record
ord-ece3b23cb42448bb85f3aee1d3ac1fa0
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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