Sodium borohydride → (7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]-oxazine-4,4'-piperidine]-1'-yl)(4-(2-hydroxyethyl)-3-methoxyphenyl)methanone

HRID 2204279Notes

Reaction equation

HRID 2204279 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:28]3[CH:29]=[CH:30][CH:31]=[C:27]3[C:8]3([CH2:13][CH2:12][N:11]([C:14]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][CH:23]=[O:24])=[C:18]([O:25][CH3:26])[CH:17]=4)=[O:15])[CH2:10][CH2:9]3)[O:7][C:6]=2[CH:32]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:28]3[CH:29]=[CH:30][CH:31]=[C:27]3[C:8]3([CH2:9][CH2:10][N:11]([C:14]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][OH:24])=[C:18]([O:25][CH3:26])[CH:17]=4)=[O:15])[CH2:12][CH2:13]3)[O:7][C:6]=2[CH:32]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 585508322-(4-(7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde

Product 1

HCID 58551847(7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]-oxazine-4,4'-piperidine]-1'-yl)(4-(2-hydroxyethyl)-3-methoxyphenyl)methanoneYield 7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2-(4-(7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde (from Step 1) was added MeOH (1 mL) followed by NaBH4 (95 mg, 2.5 mmol) and the reaction was stirred for 30 minutes at ambient temperature. After 30 minutes, the mixture was filtered and the filtrate was purified by prep-HPLC (1-99% MeOH:H2O) to give (7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]-oxazine-4,4′-piperidine]-1′-yl)(4-(2-hydroxyethyl)-3-methoxyphenyl)methanone (16 mg, 7%). ESI-MS m/z calc. 452.2, found 453.2 (M+1)+. Retention time: 2.91 minutes (4.5 min run).

Workup

  1. waitAfter 30 minutes
  2. filtrationthe mixture was filtered
  3. customthe filtrate was purified by prep-HPLC (1-99% MeOH:H2O)

Sources & evidence

ORD record
ord-aad2b72b1a4b414c922c6267cf982181
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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