Hydrochloric Acid → HCID 54671219, compound

HRID 1908169Notes

Reaction equation

HRID 1908169 reaction equation
[CH:1]([O:4][C:5]1[CH:32]=[CH:31][C:8]([C:9]([N:11]2[CH2:16][CH2:15][C:14]3([O:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[N:18]4[C:26]([C:29]#[N:30])=[CH:27][CH:28]=[C:17]34)[CH2:13][CH2:12]2)=[O:10])=[CH:7][C:6]=1[CH3:33])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>CO.Cl[Co]Cl>[NH2:30][CH2:29][C:26]1[N:18]2[C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[O:21][C:14]3([CH2:15][CH2:16][N:11]([C:9]([C:8]4[CH:31]=[CH:32][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[C:6]([CH3:33])[CH:7]=4)=[O:10])[CH2:12][CH2:13]3)[C:17]2=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 58550907HCID 58550907, compound

Product 1

HCID 54671219HCID 54671219, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1′-(4-isopropoxy-3-methylbenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbonitrile (255 mg, 0.572 mmol) in MeOH (15.3 mL) at 0° C. was added dichlorocobalt (149 mg, 1.14 mmol) followed by portion wise addition of NaBH4 (216. mg, 5.72 mmol). The reaction mixture was allowed to stir for 15 minutes at room temperature before it was cooled to 0° C. and acidified with 1M HCl. The solvent was removed under reduced pressure, and the residue was partitioned between EtOAc (50 mL) and aqueous saturated NaHCO3 (15 mL). The aqueous phase was extracted with EtOAc (2×50 mL). The combined organic phases were dried with Na2SO4, filtered and concentrated to give (1-(aminomethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-isopropoxy-3-methylphenyl)methanone (170 mg, 67%). ESI-MS m/z calc. 445.6. found 446.5 (M+1)+; Retention time: 1.45 minutes (3 min run).

Workup

  1. temperaturewas cooled to 0° C.
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between EtOAc (50 mL) and aqueous saturated NaHCO3 (15 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6638aa4031b244c0af50fa8bde138a89
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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