HCID 68469537, compound → HCID 69285699, compound

HRID 2225143Notes

Reaction equation

HRID 2225143 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][C@@H:12]1[CH2:21][OH:22])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:10][C@H:11]1[CH2:20][CH2:19][C:14]2([O:15][CH2:16][CH2:17][O:18]2)[CH2:13][C@@H:12]1[CH2:21][OH:22]

Participants

4

Reactant 1

HCID 68469537HCID 68469537, compound

Product 1

HCID 69285699HCID 69285699, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Preparation A4, Step 4: A solution of (7R,8S)-8-(S-1-Phenyl-ethylamino)-1,4-dioxa-spiro[4.5]decane-7-carboxylic acid ethyl ester (55 g, 0.165 mol) in ether (300 ml) is cooled to 0° C. in an ice bath and treated slowly with LAH (12.5 g, 0.32 mol). After the addition is complete the mixture is stirred for an additional 45 mins and then quenched by drop-wise addition of 12 ml of water followed by 50 ml of 1 N NaOH (caution: vigorous foaming). The resultant suspension is stirred in the ice bath for 1-2 hours to give a granular white suspension which is filtered on a buchner funnel. The solid is washed with ether and the combine ether filtrates are concentrated to give 48 g of the alcohol as a colorless syrup. This is used without further purification. A solution of this alcohol (42 g, 0.14 mol) in 500 ml of MeOH was treated with 13 g of 20% Pd(OH)2/C and hydrogenated overnight at 55 psi. The mixture was filtered through Celite and concentrated on a rotary evaporator to give ((7S,8S)-8-Amino-1,4-dioxa-spiro[4.5]dec-7-yl)-methanol as a syrup. This was used without further purification. 1H NMR (300 MHz, CDCl3) δ (TMS): 3.99-3.92 (bm, 4 H), 3.84 (dd, J=3 Hz, J=12 Hz, 1 H), 3.67 (dd, J=5 Hz, J=12 Hz, 1 H), 3.27 (m, 1 H), 2.51 (bs, 3 H), 1.67-1.55 (m, 7 H).

Workup

  1. customThis is used without further purification
  2. filtrationThe mixture was filtered through Celite
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-ff8135acf9fa4e8d90436d8215c372f8
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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