Potassium Hydroxide → HCID 59447818, compound

HRID 1045350Notes

Reaction equation

HRID 1045350 reaction equation
[CH:1]1([CH2:4][C:5]2([C:17]([O:19]C)=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]2)[CH2:3][CH2:2]1.[OH-].[K+]>CO.O>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)([C:17]([OH:19])=[O:18])[CH2:6]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59447841HCID 59447841, compound

Product 1

HCID 59447818HCID 59447818, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared according to general procedure B described in connection with Scheme 2. 1-t-Butyl 3-methyl 3-(cyclopropylmethyl)pyrrolidine-1,3-dicarboxylate (1.00 g, 3.5 mmol.) was dissolved in 2 mL MeOH and a solution KOH (0.59 g, 10.6 mmol.) in 2 mL H2O was added. The reaction mixture was microwaved at 130° C. for 30 min. The methanol was evaporated and 10 mL of 10% KHSO4 solution was added to the residue. The acid was extracted with EtOAc (2×20 mL). The combined organic fractions were dried over Na2SO4; evaporation of solvent gave 0.98 g of the desired product as orange oil which crystallized on standing (quantitative yield). 1H NMR (400 MHz, CDCl3): δ 3.81-3.93 (m, 1H), 3.36-3.44 (m, 2H), 2.28 (d, 1H), 2.33-2.46 (m, 1H), 1.83-1.91 (m, 1H), 1.60-1.70 (m, 2H), 1.45 (s, 9H), 0.62-0.75 (m, 1H), 0.42-0.50 (m, 2H), 0.05-0.12 (m, 2H); MS (ESI) m/z: Calculated for C14H23NO4: 269.2. found: 292 (M+Na)+.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was microwaved at 130° C. for 30 min
  3. customThe methanol was evaporated
  4. addition10 mL of 10% KHSO4 solution was added to the residue
  5. extractionThe acid was extracted with EtOAc (2×20 mL)
  6. dry with materialThe combined organic fractions were dried over Na2SO4
  7. customevaporation of solvent

Sources & evidence

ORD record
ord-628673b1dd2e4de2abf46269c1157761
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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