Hydrochloric Acid → HCID 68681207, compound

HRID 2267105Notes

Reaction equation

HRID 2267105 reaction equation
[N:1]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([O:18]C)=[O:17])=[CH:8][CH2:7]2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[C:23]([O:22][C:20]([N:1]1[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH2:7]2)[CH2:3][CH2:2]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59600625HCID 59600625, compound

Product 1

HCID 68681207HCID 68681207, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the methyl ester (B1) (1.59 g, 4.66 mmol) in MeOH (20 ml) was heated with 6N NaOH (2 ml) at 65° C. for 2 h. The reaction mixture was cooled with in an ice-bath, its pH was adjusted to ca. 5 with 0.5N HCl, and extracted with dichloromethane three times. The combined extracts were dried with sodium sulfate, filtered and concentrated to give 1′-(tert-butoxycarbonyl)-2H-spiro[naphthalene-1,4′-piperidine]-4-carboxylic acid. LC-MS: m/e=344.0 (M+H), 288.0 (M+H—C(CH3)3), 244.0 (M+H−Boc). Rt=3.29 min. 1H-NMR (500 MHz, DMSO-d6): 8.05 (dd, 1 H), 7.80 (d, 1 H), 7.68 (t, 1 H), 7.46 (t, 1 H), 6.74 (s, 1H), 4.03 (m, 2 H), 3.71 (s, 2H), 3.4 (m, 2H), 2.21 (td, 2H), 1.46 (s, 9H), 1.45 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled with in an ice-bath
  2. extractionextracted with dichloromethane three times
  3. dry with materialThe combined extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c6cebe28e614fd5a8f4285e4a801167
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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