HCID 68469537, compound → HCID 69285699, compound

Participants

Reaction Steps

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).

Provenance & Evidence