Sodium Hydroxide → HCID 67996200, compound

HRID 1615139Notes

Reaction equation

HRID 1615139 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C[O:26][C:27](=O)[CH2:28][C:29]1([CH2:42][CH:43]=O)[CH2:41][CH2:40][C:32]2([O:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][O:33]2)[CH2:31][CH2:30]1.[OH-].[Na+]>O1CCCC1.C(O)C.O.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:43][CH2:42][C:29]3([CH2:41][CH2:40][C:32]4([O:33][CH2:34][C:35]([CH3:39])([CH3:38])[CH2:36][O:37]4)[CH2:31][CH2:30]3)[CH2:28][C:27]2=[O:26])[CH3:9])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 86668371HCID 86668371, compound

Product 1

HCID 67996200HCID 67996200, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-(4-Bromo-phenyl)-ethylamine (0.17 mL), sodium triacetoxyborohydride (0.25 g), and acetic acid (0.07 mL) are added in the given order to a solution of [3,3-dimethyl-9-(2-oxo-ethyl)-1,5-dioxa-spiro[5.5]undec-9-yl]acetic acid methyl ester (0.35 g) in tetrahydrofuran (5 mL) at room temperature. The resulting mixture is stirred at room temperature overnight. Water (5 mL) and 1 M aqueous NaOH solution (5 mL) are then added and the mixture is stirred for another 20 min. The mixture is extracted with tert-butyl methyl ether, and the combined extract is washed with water and brine. After drying (MgSO4), the solvent is evaporated to give an oil that is treated with a mixture of water and ethanol to precipitate the title compound. Yield: 0.29 g (ca. 70% pure); Mass spectrum (ESI+): m/z=450/452 (Br) [m+H]+.

Workup

  1. stirringthe mixture is stirred for another 20 min
  2. extractionThe mixture is extracted with tert-butyl methyl ether
  3. extractionthe combined extract
  4. washis washed with water and brine
  5. dry with materialAfter drying (MgSO4)
  6. customthe solvent is evaporated
  7. customto give an oil that
  8. customto precipitate the title compound

Sources & evidence

ORD record
ord-2f0d8fe91c174fde842f080094f69028
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

Loading…